What-If Before Why-Not
Evaluate a disruptive idea by imagining its upside first, then treat the objections as your build list.
- Difficulty
- Easy
- Time to result
- ~days to results
- Steps
- 4
- Confidence
- 95%
When a new idea appears, people instinctively generate "why not" objections (it's too expensive, the tech isn't ready, users won't trust it). Schillace argues you must first sit with the "what if this works" question long enough to see the size of the prize. Only once the upside is real do the why-nots become useful — they convert from reasons to quit into an ordered list of problems worth solving.
Origin
Sam Schillace's own heuristic, developed building Writely (the origin of Google Docs) and refined across his career; he explicitly connects it to Elon Musk's first-principles reasoning on SpaceX and Tesla as illustrations.
Core principles
- 01Every new thing is threatening because it forces a binary choice: either you're wrong or it's wrong, and humans are storytellers who rationalize.
- 02Why-not questions are real problems but they are terminal if asked first — they kill the idea before its value is seen.
- 03What-if questions are generative: they extend the curve and reveal implications.
- 04It is better to be optimistic and wrong than pessimistic and right — there is little prize for pessimism.
- 05The order you encounter value vs. difficulty matters; seeing the value first is what motivates you to solve the hard part.
How to run it
- 1
Catch the why-not reflex
Notice the objections that arise immediately — 'the browser can't do this', 'people won't trust the cloud', 'what about no connectivity on a plane'. Name them as why-not questions rather than treating them as verdicts.
Pro tip Listen for dismissive keywords like 'it's just a toy' — that specific word often signals something real and threatening that critics can't argue against on merit.
- 2
Force the what-if
Deliberately ask 'what if this actually works?' and use imagination to extend the trend: what becomes possible, how big is the change, what are the second-order implications. Suspend disbelief long enough to size the prize.
Pro tip Frame the biggest version: for generative AI, 'what if this is the second industrial revolution — a surplus of cognitive energy beyond our brains, like water wheels gave us physical energy'.
Watch out Dumb ideas also look dumb at first, so the test isn't foolproof — pair the what-if with a genuine user-value check.
- 3
Demand a real user-value what-if
Only stay optimistic if you can articulate concrete user value in the best case. If the strongest 'what if it works' still describes a world you don't want (Schillace's crypto example: 'then I have to run upsec on my personal finances — that sounds dystopian'), the pessimism is justified — drop it.
Watch out Cool technology with no clear end-user value proposition is a signal to walk away, no matter how much marketing you could pour in.
- 4
Convert why-nots into the problem list
Once the what-if is real, take the original objections and reframe them as the concrete engineering problems to break down and attack — 'why isn't payload-to-space as cheap as it could be?' becomes the work plan.
Pro tip This is where first-principles thinking plugs in: with the what-if locked, ask 'how much would this cost if we started over?' and question each assumption in the way.
In the wild
Schillace and his co-founders saw two people could edit the same server document (the what-if: real-time collaboration in a browser is amazing) before they understood how brutally hard the merge problem was. Had they hit the difficulty first, the why-not ('three-way merge in inconsistent browser DOMs is too hard') would likely have killed it.
→ They were motivated by the seen value to solve the merge problem; Google Docs now has billions of users. Schillace calls the lucky order 'a good counter-example of the optimistic/pessimistic perspective'.
Schillace spent real time on crypto asking his what-if honestly and concluded that even in the best case he couldn't name user value he'd want. The strongest positive scenario felt dystopian to him.
→ He stayed a pessimist on crypto specifically because the what-if failed the user-value bar — showing the framework can validly say no.
Common mistakes
Asking why-not first
Leading with objections kills disruptive ideas in the crib because the more disruptive an idea is, the dumber and more threatening it looks at first.
Staying optimistic with no user-value story
Optimism untethered from concrete user value is carelessness; the what-if only counts if it describes a world users would actually want.
Is it for you?
Best for
Product builders, founders, and operators deciding whether a genuinely new/disruptive idea is worth pursuing when the room is full of reasons it can't work.
Not ideal for
Incremental features or well-understood problems where the value is obvious and the real work is execution, not conviction.
From the transcript
“I call these why not questions people ask these why not questions a lot”
“the more interesting ones are the what if questions like what if this does work”
“it's much better to be optimistic and wrong than pessimistic and right”
“what if this is actually really the Second Industrial Revolution where in the first one we had a surplus of physical energy Beyond just our…”
“for like crypto I was always like what if it works like then I have to run upsc on my personal finances that sounds dystopian”
“if we understood how hard the collaboration piece would have been first without understanding that value might have been like ah it's not worth it”
From the episode
How to be more innovative
Sam Schillace (Microsoft deputy CTO, creator of Google Docs)